Former Yankees target Alex Bregman still seeking long-term contract

With spring training fast approaching, the free-agent market is still active, and one of the biggest names available is Alex Bregman. The former Astros third baseman remains unsigned, holding out for a long-term deal. While teams like the Cubs, Red Sox, Blue Jays, Tigers, and his former club have been linked to him, the Yankees have not shown serious interest. But should the Yankees reconsider?

According to CBS, Bregman is reportedly seeking a six- or seven-year contract, a demand that has kept some teams hesitant. However, if there’s one organization that knows how to structure long-term deals to lower payroll impacts, it’s the Yankees. They’ve done it before with Aaron Hicks, DJ LeMahieu, and most recently, Max Fried.

Why the Yankees should consider Alex Bregman despite payroll concerns

New York’s payroll strategy for 2025 is clear: stay under the Cohen Tax threshold of $301 million. According to Spotrac, the Yankees are roughly $20 million below that mark, making a big free-agent signing unlikely—unless salary is cleared. That said, the front office values financial flexibility, particularly with the trade deadline in mind.

But here’s the case for Bregman: if the Yankees structured a contract in their usual fashion, they could make it work. A hypothetical seven-year, $175 million deal could be backloaded, with a lower CBT hit in the early years and escalating salaries as players like LeMahieu, Giancarlo Stanton, Marcus Stroman, Gerrit Cole, and Carlos Rodón come off the books. By 2029, only Fried and Aaron Judge would have guaranteed contracts.

If the Yankees are serious about maximizing their championship window, Bregman is exactly the kind of player who could help them right now. New York lacks an elite third baseman, and Bregman’s combination of power, plate discipline, and postseason experience would be a perfect fit. His presence would also deepen the Yankees’ lineup, reducing the pressure on Aaron Judge and Juan Soto.

Yankees Go Yard’s Thomas Carannante proposed an idea that could make Bregman’s contract feasible for New York, the Yankees could spread out the financial impact by structuring Bregman’s deal with a signing bonus and lower CBT hit in 2025, followed by higher salaries in later years. This approach would allow New York to keep payroll flexibility while strengthening their roster for an immediate championship push.

Of course, the Yankees have avoided short-term, high-AAV deals, which is why teams like the Cubs and Red Sox have pursued Bregman more aggressively. The Astros reportedly had a six-year offer on the table, and Detroit has also been linked. If New York went to seven years with a structure that kept their tax hit manageable through 2028, they could land Bregman while keeping financial flexibility.

Would it be ideal? Maybe not. But the Yankees can afford it, and their window to win is narrowing. Heading into 2025 with unresolved roster holes, they’ll once again risk their season unraveling at the worst time. Bregman is available, and with the right approach, the Yankees could make it work—just as they have in the past.

What do you think? Leave your comment below.